I guess you and I are just going to have to disagree because I just can't stand country music, I'll take the folk stylings of Stan Rogers any day. Plus he died in a boat fire; i don't know why but that just feels like a really Canadian kind of death to me.
Nobody here has bothered to maximize the 'ghey'.
This may depress you (or you may not care), but for a huge number of folks (aged over 40, anyway) in the US, Anne Murray is the singer most associated with Canada. And for younger generations, leaving Quebecoise Celine out, Shania Twain was until the Biebs came along.
Taylor Mitchell, 19-year-old Canadian folk-pop singer killed in 2009,
KILLED BY PACK OF COYOTES WHILE HIKING IN NOVA SCOTIA. Now that's fucking Canadian.
Also, Geddy Lee.